May's Fuckboy of the Month was Mr. Big from "Sex and the City." Keep up with the entire series here and vote on July's fuckboy in the comments section or WiR Facebook page.

As many of you probably know, I've been rewatching and recapping "Gilmore Girls" since August 2017. I forget why I decided to do it (a Sisyphean complex, most likely), but I definitely regret it; "Gilmore Girls" is not a good show. Everyone is white, the direction and "cinematography" are meh/whatever, and the seasons are all too long, thus resulting in tons of filler episodes where nothing of consequence happens. (Don't get me wrong; I still love it. I'm just 100% aware that there are better ways to spend my time.)

The most shocking aspect of the show on rewatch is how horrible every character is. When you think of Lorelai (Lauren Graham), do you picture a strong, independent woman and good mom? WRONG. She's a selfish cunt. Would you describe Rory (Alexis Bledel) as smart, cool, and interesting? If so, you're wrong again. She has zero personality and is most likely a shit journalist. Everything I remembered from watching this show as a 16-year-old moron (or college-aged stoner) was a lie, especially the allure of the male characters.

After careful consideration, I am positive there isn't a single dude (minus Kirk) on this show that doesn't exude a strong fuckboy aura. While I would love to dissect each one, I'm going to stick with six of the most prominent: Dean Forester (Jared Padalecki), Jess Mariano (Milo Ventimiglia), Logan Huntzberger (Matt Czuchry), Luke Danes (Scott Patterson), Christopher Hayden (David Sutcliffe), and Richard Gilmore (Edward Herrmann). (That's right, I said it: Richard fucking Gilmore.)

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I like that Luke is a dick to Dean for no reason in this episode.

Dean Forester

Despite what some may say, Dean established his fuckboy status long before he cheated on his wife with Rory at the end of Season 4. When we first meet him, he's a legitimately nice guy, new to Stars Hollow by way of Chicago. He understands Rory's pop culture references and gets his rocks off simply by watching her read. He seems genuinely intrigued and expresses his interest in nice, nonthreatening ways. He makes Rory a leather bracelet for her birthday, (reluctantly) takes her to her school dance, and sticks around even after Lorelai unnecessarily freaks out because she thinks he and Rory fucked.

Everything is going swimmingly until Season 1, Episode 16 when Dean tells Rory he loves her (while wearing a ribbed, forest green turtleneck) and she isn't ready to say it back. A nice guy might feel disappointed, but would ultimately understand and respect her request for some time to think. Instead of doing this, Bowl Cut unleashes his pettiness by throwing a temper tantrum and ending the relationship.

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In subsequent seasons, Dean trades in his turtlenecks for puka shell necklaces.

After Rory and Dean get back together at the end of Season 1, the dynamic is totally different. Dean is embarrassingly insecure, whiny whenever Rory prioritizes anything over him, and irritatingly cryptic about his feelings. Instead of straight-up asking her if she wants to suck Jess's dick, Dean pouts and seeks reassurance from Lorelai. Rory definitely treats him poorly, but when he finally breaks up with her in dramatic fashion at the dance marathon, it's hard to feel sorry for him.

Oh, and then in Season 4, he is an emotionally abusive philanderer. It's all so disgusting and I hope he dies a long, slow death. When he returns in "A Year in the Life," we find out he's married to someone named Jenny, lives in Scranton, and is expecting his fourth child ... so I guess karma caught up with this motherfucker.

Rory---Jess-Let-Me-Hear-Your-Balalaikas-Ringing-Out-Gilmore-Girls-1
Jess redeems himself in Season 6 when he calls Rory out on her nonsense.

Jess Mariano

Jess, Rory's second boyfriend, is better than Dean in some ways, in others, much worse. He's definitely still a fuckboy, but a slightly different breed. He connects with Rory over music and movies and obviously does care about her, but he's also emotionally stunted and extremely self-centered. Before they actually start dating, his behavior is pretty typical for any teen dude. He's a surly, monosyllabic little pissant, but he doesn't purposely fuck with her feelings. In retrospect, I think he probably treats her much better than she treats him.


After they make things official, the situation begins to deteriorate. Jess isn't used to having someone check up on him and he often forgets to solidify plans and keep Rory informed of his schedule. He sometimes refuses to acknowledge her anger and doesn't do a great job of expressing his feelings. Remember when he shows up for dinner at Emily Gilmore's (Kelly Bishop) house with a black eye? Instead of telling Rory that he got beaked by a swan, he lets her hypothesize and work herself up into a frenzy over whether or not his injury is from a fight with Dean.

When Jess finds out he's not matriculating and can't attend the prom, he doesn't share that information with Rory, either. He bottles everything up and then flips out when Rory won't have sex with him at some random house party. It's clear, based on the way he mutters, "You didn't do anything," after she asks what she did wrong and runs out of the room crying, that Jess isn't mad about the lack of sex. He's angry about his school situation and unfairly directs his frustrations onto Rory. Regardless, it's unacceptable and disgusting. I don't blame Dean for punching him and breaking all of Kyle's mom's Hummel figurines.

Instead of apologizing to Rory and explaining why he's actually upset, Jess skips town without a word. He calls her a few times after leaving, but doesn't say anything when she picks up the phone. In Rory's first year of college, he shows up unexpectedly more than once, professing his love for her and trying to win her back, but she swiftly dismisses his advances.

Jess-and-Rory-Howl-Gilmore-Girls
If only things could have stayed cute like this forever.

When Jess returns in Season 6, when Rory's on hiatus from Yale, he redeems himself by showcasing true vulnerability. Has Jess begun seeing a therapist?! He tells her he couldn't have written "The Subsect" without her and presses Rory to reconsider her time away from school. Later, when Rory is having issues with Logan and kisses Jess, he's relatively chill about it. He's a little upset because he still has feelings for her, but he gives her a free pass to tell Logan that something happened in order to arouse jealousy.

By "AYitL," I think it's fair to say that Jess is a reformed fuckboy. He's maintained his relationships with Luke and his mom AND he gives Rory the idea to write her book. He went through a rough period in his youth, but has since come around in a way that makes me feel okay about wearing my "Team Jess" pin. Tbh, he's way too good for Rory at this point. I hope Jess finds a nice woman who likes Dinosaur Jr. and owns an indie bookstore in upstate New York. He didn't deserve it as a teenager, but I think adult Jess is entitled to some happiness.

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"AYitL" Logan makes me want to puke. I didn't think it was possible to make him worse.

Logan Huntzberger

Even when the show originally aired, I was never a fan of Logan. He's the type of rich, entitled asshole that drives me to unspeakable acts of vandalism (I have dated a Logan before). He's the type of douche who always thinks he's the smartest person in the room, frequently talks down to women without even realizing it, and probably thinks a gallon of milk costs $20. He's like Lucille Bluth, but too young and smarmy to win any laughs.

From the moment he meets Rory, he feels entitled to her time and attention. It's clear that they have chemistry, but he pretends to be clueless about it when she flirts with him and tries to tease out his feelings. Finally, at Emily and Richard's vow renewal, Rory makes a move. Instead of reacting honestly with excitement or passion, Logan acts like he's doing her a huge favor. His response to her advances is like, "Ugh, making out at another wedding? I guess this is happening." He's the type of rich bad boy who is never excited because he feels like he's seen and done everything already.

When he and Rory begin to date, he jerks her around by claiming to want a casual relationship but jealously reacting when she shows up at a Quentin Tarantino-themed party with someone else (Robert "Grimaldi"). When he finally does decide to commit, he's a fucking horrible boyfriend. To his credit, he defends Rory at the awful Huntzberger family dinner, but he does it more for himself than for her. It's less about his family's snobby attitude toward Rory and more about his frustration with their unavoidable involvement in his life. He stands up to them because he doesn't like being told what to do, not because he gives a damn about how they've made Rory feel.

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Presents are all Logan is good for. Rory should sell that bracelet to a pawn shop.

After the fiasco at the Stanford Eagle Gazette, Logan steals a boat with Rory, no questions asked. A normal, supportive boyfriend would be like, "Hey, you don't normally decide to randomly steal boats. Is something wrong?" Instead, Logan just rolls with it because he doesn't understand that for some people, consequences actually do exist. I could write a book about all of his grievances.

At best, Logan is a fun, wealthy, bro-dude to hang out with when boredom strikes; at worst, he's a dangerous, destructive monster who doesn't understand how the world works for people who don't have money. He cheats on Rory and then tries to gaslight her when she calls him out on his nonsense. In "AYitL," he routinely cheats on Odette and doesn't seem to feel any remorse. When he proposes randomly at the end of Season 7 and Rory says no, he ends the relationship without a second thought. He wants everything to happen on his terms and when they don't, he loses interest. He does show some improvement over the course of the canon (Seasons 1-7), but "AYitL" brings him back to prime fuckboy. I hope he gets a rare neuromuscolar disorder and never returns to my TV.

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"Wedding Bell Blues" is one of those episodes that makes me want to scream.

Luke Danes

When I told my husband that Luke was on this list, he thought the inclusion was unjust because "He's the best person on the show and the only one who points out how shitty everyone else is." I totally get where he's coming from because I, too, have a soft spot for Luke; however, he's done many shitty things that I simply can't ignore.

Like Jess, most of Luke's fuckboy energy comes from being an emotional cripple. I don't think Luke ever means to be an inconsiderate asshole, but his lack of intentionality doesn't give him a free pass. For the first four seasons, he does many nice things for Lorelai in the hopes that she'll notice him and make a romantic move so that he doesn't have to. He acts as a no fee handyman, personal chef, therapist, and fishing instructor, only to watch her repeatedly date other men. At times, he's obviously annoyed by this and doesn't even try to hide it.

Lorelai knows he's interested and is theoretically capable of making a move, but she doesn't. Since this show strongly adheres to gender stereotypes, the onus is definitely on Luke to make something happen, but he is hopelessly incapable. After four-plus years of nothingness, Luke finally takes the first steps toward emotional maturity with the assistance of a few self-help tapes from Stars Hollow Books.

After he finally professes his feelings and receives reciprocation from Lorelai, their relationship rapidly progresses. Luke tells her about the horoscope, they fuck, and he begins to make small changes to help integrate Lorelai into his life. Red flags start to pop up whenever Luke is forced to share something about his past experiences or current desires. He has difficulty telling Lorelai about his "dark day," aka the anniversary of his dad's death. Instead of opening up, he shuts her out and treats her like garbage.

At Emily and Richard's vow renewal, he storms out after the Christopher incident, refuses to talk to Lorelai, and creates a huge situation out of something that might have been relatively minor had he actually talked through it with her. I suffer from some of the same issues that Luke does, so I understand what he's struggling with, but I don't find his behavior acceptable ... especially for a person in his thirties. He's one of those dudes who thinks shit like, "This is just how I am and I'll never change" instead of actively working toward self-improvement. Ignoring someone because you don't feel like talking isn't an acceptable adult coping mechanism.

April-and-Luke-Gilmore-Girls
April is totally fine ... it's Luke's treatment of her that is problematic.

When Luke finds out about April in Season 6, he either a) doesn't know how to tell Lorelai or b) worries that telling her will ruin their relationship. Instead of seeking outside advice, Luke chooses to pretend that the problem doesn't exist. Of course, everything blows up in his face when Lorelai finds out about April randomly and is crestfallen to discover that Luke has known about her existence for months. At this point, Luke and Lorelai are engaged ffs! If he still doesn't feel comfortable sharing difficult but basic information with her at this point, how the hell can the relationship realistically proceed?

And of course, the situation devolves after this revelation. Luke has no idea how to integrate April into his life with Lorelai, so he doesn't even try. He kowtows to Anna's demands without realizing that by doing so, he's deeply hurting the person who is supposed to be most important to him. His actions are without animus, but his complete lack of awareness somehow makes them more egregious.

In "AYitL," it's obvious that although Luke and Lorelai got back together and made the relationship work for many years, they still suffer from all of the same issues that were prevalent throughout the original series. Neither communicates desires clearly and instead of growing together, they've grown apart. They end up married but it's hard to feel excited about their union when it's clear they desperately need hundreds of hours of couples therapy in order to move past the problems that have been plaguing them since the beginning.

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The only good thing about this loser is the money he inherits in Season 6.

Christopher Hayden

Christopher is the most traditional fuckboy on "Gilmore Girls." As a dad, he's largely absent and only shows up for the occasional cotillion or school debate. He doesn't even make it to Rory's high school graduation! We don't really know the back story behind his lack of involvement with Rory, but it's suggested that it at least partially stems from his capriciousness.

He flirts with Lorelai pretty consistently, whether or not he happens to have a girlfriend at the time. During the aforementioned cotillion in Season 1, their chemistry is undeniable. They vibe so hard that by the end of the episode, Lorelai kisses him and invites him to spend the night. The only problem? Chris is in a serious relationship with Sherry (Mädchen Amick), something he never thought to mention when Lorelai first started giving him 'fuck me' eyes.

I've documented it on WiR many times, so you're probably aware that my main issue with Christopher is his apparent inability to wear a condom. I understand accidentally getting someone pregnant once. Shit happens and teens are dumb when it comes to safe sex. But twice?! That doesn't happen to rich white people unless they want it to happen or have some kind of impulse control disorder that prevents them from understanding how long-term consequences work.

When Sherry finds out she's pregnant and Chris's chances with Lorelai go down the toilet, he has the audacity to whine and pout, as if he's not the one responsible for everything. I know he's charming and has reformed bad boy appeal, cemented by Volvo purchase, but I truly don't understand why adult Lorelai can't move past this man-child. My vagina would have dried up as soon as his credit card got declined while trying to purchase a dictionary. No, thanks. I don't fuck with someone who is stupid enough to squander away his inheritance to the point where he can't afford to buy a book.

Lorelai-and-Christopher-Gilmore-Girls
"You are useless and no one likes you," is what I hope Lorelai is thinking.

In "Wedding Bell Blues," Chris further solidifies his fuckboy status when he gets drunk and says a bunch of bullshit to make Luke feel insecure. If he really loved Lorelai and wanted her to be happy, he would have told Emily to go away and let him watch "Teletubbies" in peace. Since Chris sucks, he follows her advice and manages to successfully derail Luke and Lorelai.

In Season 6, after turning into a relatively decent hands-off dad and human, Christopher sleeps with Lorelai, who is obviously upset, without asking any questions. A good person might have said, "Hey, Lorelai ... slow down and tell me what's wrong." Since Chris is trash, I imagine he said nothing and instead thought something like, "Dick is hard. Must fuck now."

Whoever made the decision to have Chris and Lorelai get married in Season 7 deserves to be burned at the stake. Is Chris really so ignorant that he doesn't understand Lorelai is suffering from the pain of an intense break-up and acquiescing to his advances solely because she's lonely and broken? The only thing that explains his idiocy is a raging case of neurosyphilis. "AYitL" is pretty light on Christohper details, but I imagine he's gotten at least two more women accidentally pregnant and is currently pissing away his inherited fortune on flat screen tvs and chai tea lattes.

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My love for Edward Hermann makes it hard to shit-talk Richard.

Richard Gilmore

Richard Gilmore suffers from the same misogynistic nonsense as most men his age, making him an inarguable old school fuckboy. He and Emily have a good relationship, sometimes even a great one, but it's not exactly what I would call an equal partnership. Emily chooses to stay home and run the household while Richard goes to work. Her days mainly consist of maid interviews and litigating wrongful termination suits, so nothing too strenuous. Had she wanted to, she could have gotten a job and been just as successful but instead, she adheres to the unofficial WASP handbook. Throughout their relationship, I think Richard often forgets that there's more to her than shopping trips and DAR meetings.

Throughout the series, they hit several rough patches that all stem from Richard's superiority complex. When he unexpectedly quits his job in Season 2 and doesn't tell her, she's rightfully pissed and confused. He apologizes and explains his thought process:

"You like all things planned. And then suddenly I impulsively unplan our entire future in one fail swoop. Well, I couldn't face disappointing you again."

I think it has less to do with him disappointing her and more to do with him giving up his breadwinner status. Without a regular income and his daily suit and bow tie, the dynamic with his wife is bound to change. The entire relationship will no longer be about him and his needs ... his meetings, his business trips, his daily work stresses.

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Emily 100% supports every single one of Richard's endeavors.

And of course, when Richard is retired this is exactly what happens. He feels emasculated by his lack of usefulness and doesn't know what to do with his days. Emily and the maids handle everything at home, so he's of no help to them. When he signs on as Rory's business project advisor, he finally seems happy again. He treats Emily like an annoying servant when she shows up to ask if anyone needs anything during a meeting at the Gilmore house. Instead of being annoyed by his flippant attitude, Emily seems relieved and delighted because this is the dynamic she's become accustomed to. When Richard treats her like an auxiliary character in his own life, that's how she knows all is right with the world.

In Season 4, after Richard once again neglects to tell her something important - that he's put his pension up as collateral for a business loan - their relationship begins another downward spiral. This time, it is aided by the fact that Richard has also been seeing Pennilynn Lott for secret lunches every year since he married Emily. Finally, the elder Gilmore girl has reached her breaking point and can no longer tolerate Richard's bullshit. The two officially separate and for awhile, she appears to be ~thriving~ as a single lady.

All Emily has to do is walk into the (country) club, say hello to someone, and BOOM - girlfriend has a date. Yes, she misses Richard ... but she doesn't need him to survive. It's not until he finds out about her connection with Simon McClain that Richard decides he must have Emily back. While she's in the valet line talking to Simon while waiting for someone to take her keys, Richard drives up, rams into the back of her car, and drags her away from the party. He might as well have just whipped out his dick and slapped Simon in the face with it. When Emily asks what the hell is going on, Richard mildly gaslights her and tries to insinuate that the accident was somehow her fault:

Richard: When you pull up to a valet stand, you get out of the car. You don’t dawdle.
Emily: I was waiting for someone to take my car!
Richard: Well, you wait outside the car! Everybody knows that.

Okay, guy ... sure.

Although I violently hated "AYitL," I did enjoy seeing Emily without Richard. Her grief is sad, but it's empowering to watch her take control over it and find her own happiness at the whaling museum by the season's end. It makes me wonder what her life might have been like had she married someone a bit more progressive and supportive of her dreams and desires.

Emily-Lorelai-Rory-Richards-Funeral-A-Year-in-the-Life
These women have problems, but I still think they deserve better.

The tl;dr is that the dudes on "Gilmore Girls" either a) don't know how to treat women or b) know how to treat women but are too emotionally damaged or dealing with a personality disorder that prevents them from enacting good judgment. Watching this show as a naive teenager, these men seemed like fixable heartthrobs; now, as an adult, it's clear that they're just lackluster fuckboys.